Azumolene is 1-[[[5-(4-bromophenyl)-2-oxazolyl]methylene]amino]-2,4-imidazolidinedione which is disclosed to be useful as a muscle relaxant in U.S. Pat. No. 4,049,650 issued to White on Sept. 20, 1977, the disclosure of which is hereby incorporated by reference. Example V of U.S. Pat. No. 4,049,650 discloses a method for preparing azumolene.
Dantrolene, 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione, has a chemical structure related to that of azumolene, and the sodium salt of dantrolene is commercially available as a muscle relaxant drug; see Physicians Desk Reference, 40th Edition (1986), E. R. Barnhart (Pub.), Medical Economics Company, Inc., pp. 1273-1275. Dantrolene sodium is commercially available in two forms, as an injectable, intravenous solution, and as capsules for oral administration. Commercial dantrolene sodium capsules comprise a mixture of dantrolene sodium, lactose, starch, talc, magnesium stearate and other minor ingredients contained in standard hard gelatin capsule shells; such dantrolene sodium capsules are disclosed in U.S. Pat. No. 3,689,654 issued to Conklin & D'Orazio on Sept. 5, 1972.